I was into SL for a couple years, but a bit of money into it.
My main look for my avatar was this
http://epicenic.me/enter/sites/defau...ty.preview.jpg
http://epicenic.me/enter/sites/defau...l1.preview.jpg
It took me a while to find someone who could custom make me a male skin with a womans face. (later on a shop called excess appeared that sold just that).
I faced an odd problem in SL with that look though. Everywhere I went other than GLBT spots I got mocked or rude comments made. Meanwhile other people with avatars such as furries, robots, and dragons received no such mocking (though sometimes gave it).
I stuck mainly to GLBT sites where I faces a different problem, I was alone in the world. Being what I wanted in SL means being alone among either gay men only into the manly, or TG's into looking female, with little if any in betweens. TG support sites were worse as they were all TS dominated and didn't understand my real life issues.
The few sites for crossdressing I was also disappointed as they were either forced femme (I am not into forced) or had avatars that were disturbingly childlike.
The few people I met like me either left or conformed to an existing clique. Eventually I quit, the wonder wore off and I grew tired of being alone in a crowd.
Other things TF wise I found hard if not impossible to do in SL was to put a convincing set of boobs on a manly frame. Trying a male skin on a female frame left you with impossibly scrawny arms and a small body. Putting object boobs on a male body likewise looked fake.